Parallels
by SeaSpectre160
Summary: The former billionaire playboy turned mayor by day/vigilante by night meets his former assassin turned hero ex-girlfriend's new boyfriend, the former criminal mastermind turned sort-of-hero, and finds that they have more in common than he originally thought. Sixteenth in 'Long Way Home'.


**Now I really wish Len had been with the team during 'Invasion', because I would've liked to see some interaction between him and Oliver. 'The Cold Factor' is progressing rather slowly, which is honestly a good thing since I've got job-hunting to do.**

 **DISCLAIMER: I don't own Legends of Tomorrow, Flash, Arrow, or any of their characters (or Constantine).**

 **WORD COUNT: 2917**

* * *

 _Wednesday, July 20_ _th_ _, 2016_

"So… you and Snart?"

Oliver Queen did not fake casual well, Sara decided as she took another deep swallow of beer. Gideon had cleared Len to leave the _Waverider_ a few weeks ago, and Ray and a few others insisted on throwing a party. Since Teams Arrow and Flash were also done with Damien Darhk and Zoom, it wound up being a superhero reunion slash 'we survived the latest annual disaster(s)' slash Legends' going-away party (as the time-travellers would be heading off on a new adventure the following day). S.T.A.R. Labs was filled with heroes and certain in-the-know friends and family members, in addition to three ex-villains. Ollie was chafing at the fact that Captain Cold and Heatwave knew everyone's secret identities, but the 'Legends', as Cisco dubbed them after hearing a few stories, had stood their ground and argued that the two master criminals were trustworthy. Lisa had been a bit of a surprise, claiming to have guessed Barry and Oliver's identities on her own, and she had everyone else's IDs figured out within the hour based on comparing height, build, etc. from internet photos and snippets of conversations she'd overheard over the past couple of months. Then again, she _was_ Leonard Snart's flesh and blood.

"Yes, me and Len. We've been dating for a couple weeks, now." She raised one eyebrow. "Please don't go on about how he's a dangerous criminal, and that I can do better. Because he's more than that, and he's better than you think. He's… changed… since he joined the team. Besides, you've never even met him! And most importantly, it's not your place to vet my boyfriends, Ollie."

Ollie put his hands up, a sign that he was backing down – for now. "Okay, okay. You're right, it's not my place. I'm just surprised, is all. I didn't think he'd actually stick around with a bunch of heroes once the job was done, or even for that long, really. Let alone start dating one."

She had to give him that; Sara herself had never expected it, either. She'd also never expected to find a kindred spirit in a supervillain. She looked over at him, where he was drinking his own beer while chatting with Jax and Mick. "I'll admit, I wasn't expecting it, either. But Len's… There's a lot more to him than meets the eye. Kind of like you, actually."

Oliver gave her a startled look, almost affronted by the mere suggestion that he had anything in common with the (former) career criminal.

* * *

Leonard Snart expected the third degree from a lot of the heroes when they got back home to 2016. He and Mick had half-formed a plan to skip town once Gideon cleared him, but Len couldn't bring himself to just up and ditch Sara. He figured he and his partner would say goodbye to the team, but promise to get in contact with them later (besides Sara, Len had come to enjoy Jax's company, Stein and Kendra were alright depending on the circumstances, and he'd probably get bored without insulting Ray at least once a day). But of course Barry Allen had to show up within seconds of the two of them walking off the _Waverider_ , and then he insisted on all of them coming to S.T.A.R. Labs with surprisingly little hesitation, though he kept his mask on until Mick bluntly called him by name – the kid's identity having eventually become known to the Time Masters at some point and taught to Chronos.

Then one thing led to another, and suddenly Len found himself being dragged back into S.T.A.R. Labs a few weeks later by an insistent Sara. "We're not having this party without the whole team, Len, and that includes you and Mick." So he expressed his protest by picking the lock on the main door instead of being buzzed in. The look on the former billionaire's face when Len came up from behind him was very satisfying, not just at the blatant and unnecessary breaking and entering, but how Barry then turned to Queen and told him to pay up. Apparently Len's skill/habit of waltzing into places he shouldn't have access to was becoming something of a running gag.

He spent most of the gathering in the company of his own teammates, though Barry seemed to have no problem with infringing on his space and asking him about the whole trip and how he felt about working for the good guys. Len gave him the silent treatment when those questions come up, so eventually the speedster got the hint and went away, probably to get details from the other 'Legends'. He saw Sara talking seriously with Queen, both of them glancing over at him frequently, so it didn't take a genius to figure out their topic of conversation.

So he expected it when Mayor Queen later pulled him aside to 'talk'. "Let me guess," Len pre-empted him once they were away from the crowd, "If I hurt Sara, you'll kill me? Hate to break it to you, Queen, but if I ever hurt her, she has first claim on kicking my ass, and her parents are next in line, assuming there's anything left of me once she's finished." That seemed to leave Queen temporarily speechless, something Len took no small pleasure in. "Besides, I thought we were talking about your ex-girlfriend, not your baby sister."

Queen glared at him. "What's that supposed to mean?"

"That this speech is usually something said by the father or the older brother or sister, close friends if the above aren't available. And while you certainly fall into the latter category, Sara has a cop father who _is_ available. Trust me, I've given these same threats myself."

"Really? You threaten the guys your supervillain sister dates?"

"Your baby sister used to be a vigilante just like you, the daughter and ex-pupil of the former Ra's al Ghul, and you would still do anything to protect her. I would do no less for mine. Though I loathe to admit it, Queen, we have that much in common."

And it did piss him off, having anything in common with one of the heroes that he _hadn't_ recently been fighting alongside.

Queen didn't look too happy about it, either, but seemed to accept that. Then again, the Arrow/Green Arrow had a reputation for being a bit more… morally flexible than the Flash. He _weaponised_ putting the fear of God into criminals as much as he did his arrows.

There was also something else they had in common, from what Sara had told him. He'd only gotten a second-hand account from her, because Sara was dead for that period of time. But it wasn't something he was going to ask about, because that involved bringing up something from his own past that he was still having trouble talking about.

But then Queen, damn him, brought it up, anyway. "Barry said that was why you killed your father. Because he hurt your sister."

He tried to turn that back around on the younger man. "You killed the man who hurt your sister, too – again, something we have in common."

Queen was silent for a few seconds, probably surprised that Len knew about what Ra's al Ghul did. "How much did Ray and Sara tell you?"

"Just Sara. She told me… she told me about how she died. The conversation kind of led there." He huffed. "A father puts his daughter's life in danger in order to blackmail her brother into helping him with his selfish agenda. That could apply to both Lewis Snart _and_ Malcolm Merlyn."

Queen sighed, acknowledging that.

"It sucks, doesn't it? A father should be his children's protector, not the thing they need protection from."

Queen huffed at that. "Well, the worst part is, in Malcolm's convoluted mind, he _was_ protecting Thea. He figured if he could control the League of Assassins, they wouldn't be after him anymore and wouldn't target her." Leonard gave him a disbelieving look, but Queen didn't seem to notice; his gaze, though aimed at the wall, was distant, like he was seeing something else in his mind's eye. "Malcolm seemed to equate his children being alive with them being safe and happy, and if everyone and everything they cared about was destroyed in the process, then so be it. He never took into consideration the idea that they might never agree with him. He thought that if they resisted his plans, it was because they were too immature to see the big picture, because he was the one who knew what was best for them. That's what got Tommy killed."

Len scowled. He wasn't sure which was worse: not caring at all about your kids' lives or forcing them to live without anyone or anything they loved. "So, do all your heroes have similarly screwed-up families?"

Queen sighed. "I think ours are the worst. No one else's parents have tried to destroy their kids' lives, in one way or another." He paused. "I mean, Felicity's dad is technically one of our villains, but he helped us stop Genesis, and now that he knows his daughter's one of us, he's backing off. And I don't know much about Rory's family…"

"He lost control of his fire one night and burned them alive. It was an accident, but from little bits he's told me about before that, his father might have deserved it. And that's all I'm gonna say." Queen nodded, although Len could tell he wanted to know more about the other criminal who would be time-travelling with two of his friends.

"Ollie!" The call drew their attention away from whatever might have been said next. It was Thea, who had come to the party despite having retired from the vigilante life, wanting to say goodbye to her friends on the _Waverider_ before they left. "The ladies here want to hear about that whole thing with Cupid, and you tell it best, so get over here!"

Queen shook his head. "I hope she means when Cupid first started killing people," he muttered, "because there was _way_ too much… personal crap going on the second time." To his sister he called: "Yep, coming!" But before he went to join her, Iris, Caitlin, Clarissa, and Kendra, he apparently had one last thing to say to Len. "Just… Look out for her, would you?" It was rather obvious which 'her' he was talking about. "All of them, really, but especially Sara. As deadly as she is, she's already learned the hard way that even she can be caught off-guard."

"That's an understatement," Len agreed, "I look out for my own, Queen, you don't have to worry about that."

One of his teammates _must_ have told Queen about his whole sacrifice at the Oculus (really, they'd been back in 2016 for nearly two months, now, so it was hard to believe that that tale hadn't been told at least a dozen times to _everyone_ ), because the guy didn't question it. He just nodded and went to entertain the majority of the female party guests with the story of some homicidal chick named Cupid (Len made a mental note to ask Sara and Ray if they knew that one).

Looking over the crowd gathered there, he allowed himself a mental shake of the head in disbelief at the bizarre mix of people. The Geek Squad minus Caitlin (meaning Cisco, Ray, Stein, and two Star City nerds who'd been introduced as Felicity and Curtis) were all bent over the computers, talking science. Lisa sat with them, as well, but she seemed to be more interested in flirting with Cisco and tripping him up than anything else. Len had to remind himself of the cute kid he saw in 2024 to keep himself from breaking that up. He wouldn't risk wiping his future niece out of the timeline.

In one corner, Mick and Carter sat side-by-side, silently nursing their drinks and not really talking to anyone. Mick had always preferred to sit off to the side and drink unless the conversation turned to something he actually cared to talk about, and Carter was still adjusting after Savage mind-screwed him. As long as the reincarnated hawk-god was quiet, Len knew his partner wouldn't mind the company.

Not too far away, Jax and Iris's long-lost kid brother Wally were talking animatedly about sports. It hadn't taken long for the two of them, both pretty much the same age, to hit it off.

Finally, he spotted Sara, discussing something with Rip, Barry, and Joe West. As if sensing his gaze, she looked up and met his eyes, then excused herself and walked over. "Ollie didn't try and give you the Shovel Speech, did he?"

"He tried," Len conceded, "But I told him it wasn't his place to give me one and that I was too used to giving those speeches myself to be scared of his, and the conversation kind of deviated from there."

Sara gave him an amused look. "I'd ask what you two could possibly have in common to talk about, but then again, I can think of a few things."

Len frowned at that, still not happy about having anything in common with Oliver Queen, but obviously the woman who'd dated them both would figure out a connection. "Mostly our sisters and shitty fathers. Well, in his case just his _sister's_ shitty father."

Sara leaned into him, hooking her arm around his. "I seriously hope that won't be the only topic of conversation whenever you two interact. That would be _really_ depressing."

"Very true," Len agreed, resolutely ignoring the wink Mick sent him from across the room at this so public display of affection. And glaring at Cisco when the geek lifted his phone, obviously looking to take a picture of them (luckily Felicity saw this and plucked the device out of his hands). He was still getting used to this… touchy-feely stuff, especially when other people could see it. Being open about the fact that Sara was important to him, and that he could be hurt through her, was not something that came easily to him. But what was also new for him was being around people who wouldn't use the few people he cared about against him, and here he was, surrounded by a group of people that would fight and _had_ fought to watch his and Sara's backs with no expectation of anything in return.

He wouldn't have imagined this a year ago, that he would be saving the world, dating a cop's daughter, having a civil conversation with someone as high-standing as a mayor. But then again, _two_ years ago, he also wouldn't have expected to be living in a world filled with metahumans, magic, and time-travel.

* * *

"So, what's the verdict?"

"Huh?" Oliver blinked at Felicity's question.

"Don't give me that clueless act. You drag Sara's new boyfriend, the only-recently-reformed supervillain, away for a 'chat', and you expect me to believe you weren't interrogating and/or threatening him?"

Oliver sighed. "Okay, fine, that was the plan, but it didn't actually work out that way." He shrugged. "We talked… I had a surprisingly civil conversation with a career criminal."

Felicity grinned. "Yeah, today is a weird day, huh?"

"Tell me about it. We're giving our friends a send-off before they get back on a flying time machine to who knows where – to who knows _when_. I still can't believe that this is our life, now."

"Yeah, I know, it's crazy, but seriously – what's the verdict on Sara's new fugitive from the law boyfriend? I mean, he seems to be pretty different from when he tried to shoot Barry after derailing a train, but what's your opinion?"

Oliver let out a deep breath, going back over the conversation in his mind. "He's… not what I expected, to be perfectly honest. He was quick to remind me that Sara will be the one to kick his ass herself if he hurts her, he's incredibly protective of the people he considers to be 'his', and… I think he and Sara are really good for each other."

Felicity grinned and nudged him. "You like him."

"What?"

"Admit it. You actually approve of Leonard Snart. Who would have thought?"

Oliver shrugged. Her words summed it up pretty well. Who would have thought, when he first started his crusade, that he would gain friends and allies in the form of metahumans, magic-users (besides John Constantine), and crooks? Who would have thought that he'd approve of one of said crooks getting into a relationship with one of his oldest friends?

Seriously: Who would have thought?

THE END

* * *

 **So sorry for the wait! That last scene really had me stuck.**

 **But... to make it up to you, here's a little preview of the first chapter of 'The Cold Factor'!**

 _ **The lights flickered back on, and both Snart and Rory gasped like they'd been holding their breath for several minutes (or perhaps seventy-four years). Dr. Heywood took several steps back, and Oliver found himself with a fight on his hands as Rory's fight-or-flight instinct kicked in. It was brief, however; Oliver managed to wrestle Rory back onto his chair, but then a pair of hands grabbed him and yanked him away. Oliver spun around in time to catch Snart's fist with one hand. He was ready to throw a punch of his own, but then Snart's expression cleared, like he was only just fully waking up. "Queen?" he asked, "How in the hell did you get here?"**_

 _ **Oliver let him go. "I came on a submarine with Dr. Heywood here; your ship just let us into the airlock. I don't know exactly how long the Waverider's been down here, but we followed evidence from 1942 and it's 2016 now. You two are the only ones we've found on board so far. What happened to the rest of the team?"**_


End file.
